Methyl iodide → 4-Chloro-1-methyl-1H-indole

HRID 1155692Notes

Reaction equation

HRID 1155692 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[OH-].[Na+].[CH3:13]I>C1C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[CH3:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 913454-Chloroindole

Product 1

HCID 130487594-Chloro-1-methyl-1H-indole

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 60 g of 4-chloro-1H-indole, 400 ml of benzene, 200 ml of a 50% solution of sodium hydroxide, 68 g of n-tetrabutylammonium acid sulfate and 68 ml of methyl iodide was heated at 40° C. with agitation for 4 hours and was then cooled and decanted. The aqueous phase was extracted with ethyl acetate and the combined organic phases were washed with a saturated aqueous solution of sodium chloride, dried and distilled to dryness under reduced pressure. The residue was purified by chromatography on silica gel and elution with an 8-2 mixture of cyclohexane and benzene to obtain 63.85 g of 4-chloro-1-methyl 1H-indole.

Workup

  1. temperaturewas then cooled
  2. customdecanted
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined organic phases were washed with a saturated aqueous solution of sodium chloride
  5. customdried
  6. distillationdistilled to dryness under reduced pressure
  7. customThe residue was purified by chromatography on silica gel and elution with an 8-2 mixture of cyclohexane and benzene

Sources & evidence

ORD record
ord-47383c5e405d495f90f64788292e692f
Source dataset
uspto-grants-1982_06
Patent number
US04332808

Reaction notes

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